How did some of the most successful women in the world get to where they are today?

[How do you manage to balance both]?

Mindy Grossman: First, we must give ourselves permission to step out of the self-perpetuating cycle of guilt.

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I feel like [parenthood] even amplifies [those feelings].

Is this something that Im passionate about, is it purposeful, and will I have impact?

MG: Thats been the story of my life.

Its not just one time.

Every move has been that way.

JA: How are you not scared?

MG: Each new stage holds within it some level uncertainty or fear of the unknown.

But it can also be exhilarating, and even liberating, because its filled with so much opportunity.

One of the most important decisions Ive ever made was a huge risk.

you’re free to just imagine their state of shock upon receivingthatnews!

I believed in myself enough to take a risk and go against the status quo.

When I get stuck thinking like that, I ask myself, what if?

and have a go at think of the worst things that could happen.

When I break it down, its usually worth the risk.

JA: Why do you think there are so few women in business?

Do you think its the overthinking?

MG: There are a few reasons.

There are still gender biases and double standards.

I also think [it may be due to] the fear of taking risks.

JA: Do you think [they fear the] criticism of their peers?

Or [dont believe] in their capability?

MG: Its probably a combination of things.

But there are structural issues within business and society that contribute to the imbalance.

MG: It absolutely requires looking through a bit of a different lens.

JA: Whats your boss outfit?

I pair those with bright colors, accessories and killer shoes.

Or, alternatively, I have a lot of dresses.

JA: Whats your shoe height?

Are you a 3-inch or a 5-inch?

MG: Im a 5-inch.

JA: What was your first job?

MG: Actually thats a funny story.

My first job was when I was 17.

It was the summer after my first year in college.

I decided I wanted to work in NYC, and I cant believe my parents actually let me.

I took the job, and immediately got fired.

Fortunately, I found another position where they didn’t make jumpsuits!

JA:Whats the first thing you do in the morning?

MG: My routine is unfortunately that my iPhone is right next to my bed.

And its different now that I dont have a little kid in my house.

I definitely check messages, I check my calendar, I watch Bloomberg, and I have my coffee.

And then Ill check my apps.

JA: And [do you drink] black coffee, coffee with milk and sugar?

JA: Do you eat breakfast?

MG: If I do, I generally eat fruit.

MG: One of my disappointments is that I never got to meet Steve Jobs.

I just think itd be fascinating.

JA: I agree.

Who is the woman you consider the most boss?

MG: Ive been thinking about that.

Her name is Katie Meyler.

[She was a] Time Magazine Person of The Year [with other] Ebola fighters.

Instead of running away she stayed and reported for VICE News.

Caryl Stern whos the CEO of the U.S. Fund for UNICEF is another woman whos spectacular.

Theyve really been inspirations to me.

JA: Thats great.

Whats your least favorite word or habit that people use at work?

JA: Me too.

Its all about how you look at things and how you approach problems and challenges.

I have this expression that I dont hire Eeyores, I only hire Tiggers.

I just cant be around negative energy because I dont think it does anything productive.

JA: Complete this sentenceI cant live without ___ at the office.

Youve got to have fun.

JA: Whats the perfect ending to your day?

MG: I would say the perfect ending to my day is to have dinner with my family.

We cant be together all the time, so when we are its just so enjoyable.

I commuted in some way, shape or form for 11 years.

Its such a joy to be able to spend time with family.

And our family is expanding!

This interview has been edited and condensed for clarity.